Amino acid conjugates of 1,1'-diaminoferrocene. Synthesis and chiral organization |
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Authors: | Chowdhury Somenath Mahmoud Khaled A Schatte Gabriele Kraatz Heinz-Bernhard |
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Institution: | Department of Chemistry, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada. |
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Abstract: | 1,1'-bis(tert-butoxycarbonylamino)ferrocene (6), a protected derivative of 1,1'-diaminoferrocene, has been synthesized by a very convenient method and serves as a synthon for 1,1'-diaminoferrocene. Its structure in solid state and in solution has been studied by NMR and X-ray crystallography. 1,1'-bis(tert-butoxycarbonylamino)ferrocene serves as starting material for the synthesis of amino acid conjugates of L- and D-alanine. The structures of these bioconjugates have been studied by NMR and CD spectroscopy and X-ray crystallography and reveal that the chiral organization of the podant amino acid chains is controlled by the chirality of the attached amino acid. The substituents engage in strong intramolecular H-bonding generating 14-membered H-bonded rings, a motif previously unrealized in ferrocene-amino acid and peptide conjugates. |
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